4-Methylmorpholine → 3-Phenyloxycarbonyloxymethyl-3-methyloxetane

HRID 742928Notes

Reaction equation

HRID 742928 reaction equation
[O:1]([C:8](Cl)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:11][CH2:12][C:13]1([CH3:17])[CH2:16][O:15][CH2:14]1.CN1CCOCC1>C(Cl)Cl>[C:2]1([O:1][C:8]([O:11][CH2:12][C:13]2([CH3:17])[CH2:16][O:15][CH2:14]2)=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 15891Phenyl chloroformateHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 189397703-Phenyloxycarbonyloxymethyl-3-methyloxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A 0.552 mL (4.42 mmol) sample of phenoxycarbonylchloride in 2 mL of methylene chloride was added to a solution of 376 mg (3.68 mmol) of 3-hydroxymethyl-3-methyloxetane and 60.7 mL (5.52 mmol) of 4-methylmorpholine in 2 mL of methylene chloride cooled in an ice bath. The mixture was stirred at 0° C. for 3.5 hours. The mixture was diluted with methylene chloride, which was washed with water, dried and concentrated. The crude product was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane. The solvent was removed and the product dried to afford 0.582 g of the title compound, which was taken directly to the next step.

Workup

  1. temperaturecooled in an ice bath
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel
  6. washeluting with 20% ethyl acetate in hexane
  7. customThe solvent was removed
  8. customthe product dried

Sources & evidence

ORD record
ord-41e62329d3894866b3febbc5bdbf6ca2
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

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